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Iron‐Catalyzed Ring‐Closing C−O/C−O Metathesis of Aliphatic Ethers

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Biberger,  Tobias
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Makai,  Szabolcs
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Lian,  Zhong
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Morandi,  Bill
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Biberger, T., Makai, S., Lian, Z., & Morandi, B. (2018). Iron‐Catalyzed Ring‐Closing C−O/C−O Metathesis of Aliphatic Ethers. Angewandte Chemie International Edition, 57(23), 6940-6944. doi:10.1002/anie.201802563.


Cite as: http://hdl.handle.net/21.11116/0000-0001-BF5F-F
Abstract
Among all metathesis reactions known to date in organic chemistry, the metathesis of multiple bonds such as alkenes and alkynes has evolved into one of the most powerful methods to construct molecular complexity. In contrast, metathesis reactions involving single bonds are scarce and far less developed, particularly in the context of synthetically valuable ring‐closing reactions. Herein, we report an iron‐catalyzed ring‐closing metathesis of aliphatic ethers for the synthesis of substituted tetrahydropyrans and tetrahydrofurans, as well as morpholines and polycyclic ethers. This transformation is enabled by a simple iron catalyst and likely proceeds via cyclic oxonium intermediates.